Russian Journal of Applied Chemistry, 2012, Vol. 85, No. 11, pp. 1711−1717.
Pleiades Publishing, Ltd., 2012.
Original Russian Text © A.I. Il’icheva, Yu.P. Barinova, L.N. Bochkarev, V.A. Il’ichev, 2012, published in Zhurnal Prikladnoi Khimii, 2012, Vol. 85, No. 11,
AND POLYMERIC MATERIALS
Complex of Copper(I) with Norbornene-Substituted
Pyridinylbenzimidazole Ligand and Copper-Containing
Carbochain Copolymers Based on This Complex: Synthesis,
Photo- and Electroluminescent Properties
A. I. Il’icheva, Yu. P. Barinova, L. N. Bochkarev, and V. A. Il’ichev
Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, Nizhni Novgorod, Russia
Received June 20, 2012
Abstract—New complex of copper(I) with norbornene-substituted 1-H-2-pyridinylbenzimidazole ligand was
synthesized. The compound obtained enters into a metathesis polymerization reaction to give carbochain copper-
containing copolymers exhibiting photo-and electroluminescent properties.
At present, information displaying devices based on
organic light-emitting diodes (OLEDs) ﬁ nd steadily in-
creasing use. Since the ﬁ rst reports about the high-in-
tensity electroluminescence (EL) from metal complexes
and polymeric materials, a search for new effective
electroluminescent phosphors has been continued [1, 2].
The best working characteristics are observed for OLED
devices based on complexes of platinum and iridium
[3, 4]. Platinum- and iridium-containing polymers ex-
hibiting rather effective electroluminescent properties
are known [5–8]. The advantages of polymeric emitters
over low-molecular phosphors are primarily associated
with the possibility of fabricating emission layers from
three polymers by jet printing or spin-coating without
use of expensive high-vacuum equipment. In addition,
the jet printing method can be used to create large-area
OLED devices, which can hardly be fabricated by vacu-
um techniques [3, 4].
It has been found recently that some copper(I) com-
pounds can exhibit electroluminescent properties [9,
10]. Because copper compounds have a substantially
lower cost, compared with platinum and iridium deriva-
tives, and are nearly nontoxic, the interest in copper-
containing electroluminescent phosphors has markedly
increased recently [11, 12]. However, published evi-
dence about copper-containing electroluminescent poly-
mers is scarce.
This communication reports on how a luminescent
complex of copper(I) with a norbornene-substituted
1-H-2-pyridinylbenzimidazole ligand is synthesized
and new carbochain electroluminescent copper-contain-
ing homo- and copolymers are produced on the basis of
this complex via metathesis polymerization. It is well
known that, as a rule, ring-opening metathesis polym-
erization (ROMP) reactions occur in the controlled-
living-polymerization mode and allow synthesizing
functionalized polymers with a narrow molecular-mass
distribution and prescribed molecular masses .
Therefore, this method was chosen for obtaining target
copper-containing polymeric materials.
A new norbornene-containing copper complex 2
was synthesized via functionalization of the pyridinyl-
benzimidazole ligand contained in the known copper
derivative 1 possessing effective luminescent properties
Compound 2 is a pale yellow solid substance that is
stable in air.
It was found that monomer 2 enters into a ROMP
reaction in the presence of a third-generation Grubbs